| Targets |
The primary target of 16,16-dimethyl-PGE1 is the Prostaglandin E (EP) receptor family, particularly EP2 and EP4. Like PGE1, it is a potent vasodilator and inhibitor of platelet aggregation. It also interacts with other prostaglandin receptors, as it induces contraction in various smooth muscle tissues (tracheal, bronchial, bronchiolar) that is mediated by TP receptors (thromboxane A2 receptor).
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| ln Vitro |
16,16-dimethyl-PGE1 induces human vascular smooth muscle contractions in vitro. It is 2, 3, and 6 times more potent than PGF2alpha in contracting tracheal, bronchial, and bronchiolar smooth muscle, respectively. This demonstrates its broad activity on smooth muscle across different tissues and highlights its increased potency due to the metabolic stabilization.
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| ln Vivo |
16,16-Dimethylprostaglandin E1 (1 μg/kg•min for 30 minutes) can accelerate the recovery of blood pressure and heart rate after acute hemorrhage in Sprague Dawley rats, increase catecholamine turnover, and elevate plasma levels of epinephrine and norepinephrine [1].
16,16-Dimethylprostaglandin E1 (1 microg/kg•min for 30 minutes) can accelerate the recovery of blood pressure and heart rate after acute hemorrhage in Sprague Dawley rats, increase catecholamine turnover, and elevate plasma levels of epinephrine and norepinephrine. This demonstrates its potent in vivo cardiovascular effects, likely through stimulation of sympathetic nervous system activity. |
| Enzyme Assay |
Standard prostaglandin E receptor binding assays: To determine its affinity, competitive binding assays using [3H]-PGE2 or a selective EP agonist as a radioligand on membranes from cells expressing specific EP receptors (EP1, EP2, EP3, EP4) can be used. The IC50 or Ki for 16,16-dimethyl-PGE1 at each receptor subtype can be calculated. Additionally, a smooth muscle contraction assay using isolated guinea pig tracheal rings, as described in the literature, can quantify its potency.
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| Cell Assay |
Standard cell-based assay for PGE2 activity: Several cell-based assays are available to measure the functional activity of EP receptor agonists. For instance, the inhibition of LPS-induced TNF-alpha production by macrophages can be measured. Alternatively, its effect on cAMP accumulation in cells expressing EP2 or EP4 receptors can be assessed using an HTRF cAMP kit. Briefly, cells are incubated with the compound, and the resulting cAMP level is measured as a readout of receptor activation.
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| Animal Protocol |
Animal/Disease Models: Sprague-Dawley rats[1]
Doses: 1 μg/kg•min Route of Administration: 0-30 min Experimental Results: Improved blood pressure and heart rate, improved levels of epinephrine and norepinephrine im plasma. Acute hemorrhage model in Sprague Dawley rats: Rats are bled to lower mean arterial pressure to 40 mm Hg for 30 minutes. After the hemorrhage period, 16,16-Dimethylprostaglandin E1 is infused intravenously at a constant rate of 1 microg/kg•min for 30 minutes. Blood pressure, heart rate, and plasma catecholamine levels (epinephrine, norepinephrine) are measured at regular intervals to assess the compound's cardiovascular effects. |
| ADME/Pharmacokinetics |
16,16-Dimethyl-PGE1 is a metabolically stable synthetic analog of PGE1. The addition of methyl groups at the 16-position protects the molecule from rapid oxidation by the enzyme 15-PGDH, resulting in a significantly longer in vivo half-life compared to natural PGE1. It is administered intravenously in research settings. Its distribution and elimination pathways are similar to other prostaglandins but occur on a much slower timescale.
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| Toxicity/Toxicokinetics |
Toxicity data for 16,16-Dimethyl-PGE1 is not available in the provided references. However, as a potent prostaglandin analog, it can be expected to cause classic prostaglandin-related side effects at high doses, such as hypotension, diarrhea, bronchoconstriction, and gastrointestinal issues. The specific safety profile is not provided.
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| References |
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| Additional Infomation |
16,16-Dimethylprostaglandin E is a prostaglandin. The given references refer to the (11α,13E,15R)-isomer.
16,16-Dimethylprostaglandin E1 (CAS: 41692-15-3) is a synthetic analog of PGE1 that is metabolically stable. It induces smooth muscle contractions and is 2 to 6 times more potent than PGF2alpha on respiratory tissues. Its molecular formula is C22H38O5, and its exact mass is 382.271926. |
| Exact Mass |
382.272
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|---|---|
| CAS # |
41692-15-3
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| PubChem CID |
5283058
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
540.9±50.0 °C at 760 mmHg
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| Flash Point |
295.0±26.6 °C
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| Vapour Pressure |
0.0±3.3 mmHg at 25°C
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| Index of Refraction |
1.539
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| LogP |
2.94
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
27
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| Complexity |
497
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| Defined Atom Stereocenter Count |
4
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| InChi Key |
RQOFITYRYPQNLL-ZWSAOQBFSA-N
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| InChi Code |
InChI=1S/C22H38O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h12-13,16-17,19-20,24-25H,4-11,14-15H2,1-3H3,(H,26,27)/b13-12+/t16-,17-,19-,20-/m1/s1
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| Chemical Name |
7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopentyl]heptanoic acid
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| Synonyms |
16,16-dimethyl-PGE1
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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